


The Ride Home

by SinQueen69



Series: Requests [41]
Category: Teen Wolf (TV)
Genre: Anal Beads, Ball Gag, Bondage, Car Sex, Cock Cage, Crying, Dirty Talk, Dom Derek Hale, Dom/sub, Don't copy to another site, Forced Orgasm, Fucking Machine, M/M, Nipple Clamps, Nipple Play, Overstimulation, Prompt Fill, Punishment, Sex Toys Under Clothing, Sub Stiles Stilinski, Teasing, Verbal Humiliation, Vibrating anal beads, hole spanking
Language: English
Status: Completed
Published: 2020-06-14
Updated: 2020-08-07
Packaged: 2021-03-03 22:54:11
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 1,482
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24723352
Author URL: https://archiveofourown.org/users/SinQueen69/pseuds/SinQueen69
Summary: Anon from my request form wanted: Maybe with Stiles and Derek at dinner in a nice restaurant but Stiles has nipple clamps and vibrating anal beads in so Stiles is trying to be quiet. Then after dinner Derek takes Stiles home and takes the bumpy road home and Derek is teasing Stiles by saying how much of a slut he is and then they fuck.+Anon Tumblr who wanted more cock cages+anon from my request form wanted: You write cock cages so well and it’s my number one kink hehe, I’d love to see more of it in the sterek pairing, I find subby stiles so cute. Maybe have lots of degradation and humiliation, and some dumbification if you’re comfortable writing that. Either way i love all of your stuff and will read whatever you wish to share :)Chapter 2- Requested
Relationships: Derek Hale/Stiles Stilinski
Series: Requests [41]
Series URL: https://archiveofourown.org/series/1618726
Kudos: 534





	1. Chapter 1

Derek didn’t even bother to hide his smile as he watched as Stiles shifted in his seat across from him, again. 

“Comfortable?” Derek asked innocently as he nudged the dial on the remote in his pocket and watched as Stiles’ jolted, knee hitting against the underside of the table. 

“Very,” Stiles replied through gritted teeth as he stabbed a piece of the dessert the two were sharing. 

“That’s good to hear, I was thinking of taking Mountain Ave back to the loft.” Derek smoothed his foot up Stiles’ parted legs and smiled when Stiles inhaled sharply when the older man’s foot pressed against his crotch. 

“M-Mountain Ave, y-yeah, okay.” Stiles stammered out as he shifted again and Derek saw understanding dawn in Stiles’ eyes as he realized that Mountain Ave was the bumpiest road in town and he shuddered. 

“Good,” Derek watched as Stiles leaned forward to scoop up the last bit of dessert, shuddering again and Derek took a sip of his drink when he saw two bulges pressing against Stiles’ shirt reminding Derek of what was hidden underneath. 

Derek was a gentleman and escorted his partner to their car when they finished their rather long and drawn out dinner out. Stiles wiggled in his seat as Derek turned down Mountain Ave and clutched at the door handle and let out a loud gasp when they hit the first bump.

“You okay babe?” Derek teased as he hit another bump making Stiles arch in his seat.

“You are an evil, evil person.” Stiles gritted out before keening when they hit multiple bumps and Stiles clung to the door handle and seatbelt. Derek removed one hand from the wheel and cupped his boyfriend’s crotch. 

“You’re so wet, like a girl, goddamn you’re such a slut.” Derek laughed as he squeezed the wet fabric around Stiles’ cock as Stiles keened and rutted up against his hand helplessly. 

“Maybe I should treat you like a proper slut,” Derek turned down a dirt road and pulled off to the side, cutting the engine. 

“Do you want that, do you want me to fuck you like a slut?” Derek growled as he reached forward, yanking up Stiles’ shirt to expose his clamped nipples. They were hard, erect and a puffy red that were being squeezed constantly by the rubber-tipped clamp. Stiles keen and jerked when Derek flicked the clamps with a smirk on his lips. 

“Please fuck me!” Stiles whimpered before crying out when Derek twisted the clamps making him arch and rut his hips up again.

“Ask me properly,” Derek reminded as he eased up on the clamps. 

“Please Sir, please fuck me like a slut!” Stiles fought back a sob as his clamped nipples throbbed as his caged cock strained against the fly of his pants. 

“Better, open your door and bend over the seat,” Derek ordered as he undid his seatbelt, leaving his side of the car as Stiles whined and scrambled to do as he was told. 

“I will admit, you stayed very quiet throughout dinner, even with these vibrating inside of your greedy hole,” Derek was impressed by his lover’s restraint at the restaurant but all of that was gone when Derek pressed his thumb against Stiles’ pucker. 

Derek hooked his finger around the small rubber circle that was attached to a string that led into Stiles’ hole and tugged. Stiles cried out into the leather car seat he was bent over as a large anal bead ever so slowly popped out of it, the ball was still buzzing from the level of vibration it had been set on. 

Stiles lifted his hips, going onto his tip-toes as Derek pulled the next vibrating bead out of him, forcing his rim to stretch wide again. Derek rubbed his thumb over Stiles’ leaking cock teasingly before pressing down as he pulled out the third and final bead, grunting when Stiles wailed into the car seat unable to stop himself as his rim clenched on reflex. Stiles’ caged cock dripped from where it was pressed against the side of the car seat Stiles was bent over. 

“Such a slut,” Derek said fondly as he planted a kiss to the small of Stiles’ back, his shirt having been rucked up by this point. 

“Now be a good slut and hold your hole open for me to fuck.” Derek was quick to unzip his pants and slick up his cock with the packet of lube he had brought in preparation. 

“Yes Sir,” Stiles breathed out as he reached around and used his fingers to tug his well-stretched hole open wider for Derek, feeling loose and relaxed from his intense orgasm. 

Stiles moaned happily as a familiar girth and weight was pushed slowly but steadily into him as the older man grasped his hips not stopping until his balls settled against Stiles’ ass. Derek used one hand to pull Stiles’ upper body up so he could grope and play with Stiles’ clamped nipples as he began to thrust into him from behind. 

Stiles shuddered and whined, as he tended to do when Derek took him from behind like this and the fact they were doing this on the side of the road made it so much hotter. 

“Tell me slut, do you want me to come in you?” Derek already knew the answer but loved hearing it nonetheless. 

“Yes! Please, Sir! Please come inside of your slut!” Stiles begged as he did his best to clench around Derek’s cock. 

Derek moaned directly into Stiles’ ear as his body stilled from where he was buried deep in Stiles’ ass before he was coming making Stiles shiver and gasp in pleasure. 

“I think you can hold my load in your slutty little hole until we get home, don’t disappoint me and don’t even think about touching your pathetic little cock.” Derek ordered when he pulled out of Stiles’ messy hole and Stiles clenched his muscles as Derek pulled his clothes back into place. Stiles’ caged cock jerked between his thighs as the rough denim of his jeans rubbed over them. 

“Yes Sir,” Stiles whimpered as he did his best to get comfortable back on his seat as Derek started the car with a smug smirk on his lips.


	2. Chapter 2

**Summary for the Chapter:**

> Request Anon: Thank you for taking your time to post all of these for us!! I loved ‘The Ride Home’, would totally read a part 2💗 Maybe one day Stiles is really horny and Derek catches him trying to take his cock cage off & has to remind him of his place? Maybe by making him cum loads of times and extreme overstim since stiles was so desperate for it 🥺
> 
> +
> 
> Anon on Tumblr: Hei, I love your fics, you're an amazing writer! I had a request - Peter/Stiles or Derek/Stiles with multiple orgasms and overstimulation, where in stiles constantly tells them he cant come anymore but there are 6/7 forced orgasms. Thank you!

“Did you say something slut?” Derek asked curiously, peering up from his book when muffled noise reached his ears. Derek set his book down and leaned his elbows on his knees to inspect Stiles’ straining, vibrating body. 

Stiles’ cheeks were flushed and tear tracks were on his cheeks as he drooled around the red ball gag that was snuggly placed between his lips. Derek hummed at the mess of fresh and dry cum on Stiles’ stomach and thighs, his cock free of its usual cage. The length was an angry red and half-hard, Stiles sobbed as weak little spurts of cum spilled from the tip as his body trembled as the thick dildo he was seated on changed vibrations. 

“Don’t complain slut, you did this to yourself. I warned you not to touch your pathetic little cock without my permission. Yet you did and you’re being punished for it.” Derek scolded as Stiles let out a muffled moan as his cock twitched as it tried to rise again. 

Derek stood from his chair, walking around Stiles who was straddling a Sybian, the machine buzzing loudly as it kept the fat dildo inside of him moving constantly. Derek knew that the fake cock was pressed right against Stiles’ prostate, forcing orgasm after orgasm out of him. 

Derek squatted down behind Stiles, prying his submissive’s ass cheeks apart to get a better view of the younger man’s puffy, loose hole. Derek got a flash of inspiration on how to force more orgasms out of Stiles until the younger man was coming dry. Derek used his strength and lifted Stiles off the vibrating dildo. Stiles gasped and his body swayed before he let out a quieted cry when Derek suddenly brought his hand down hard on Stiles’ hole. Derek kept Stiles still as he squirmed each time Derek spanked the younger man’s hole. 

“Accept your punishment slut, accept your place,” Derek growled, not pausing in his harsh spanks until Stiles had fresh tears down his face. Derek checked in to make sure the red ball was still tightly held in Stiles’ hand and it was before Derek yanked Stiles back down onto the dildo. 

Stiles arched, crying out behind the gag as little drops of cum dripping out of his cock. Stiles sobbed and jerked as extreme overstimulation covered his every sense as the machine vibrated the dildo deep inside of his throbbing, aching hole. 

“You’ll think twice about touching what doesn’t belong to you won’t you slut?” Derek patted Stiles’ wet cheek before sitting back down in his chair, picking up where he left off in his book as Stiles took his punishment.

**Notes for the Chapter:**

> I've created a safe anonymous place for darker/filthy requests.
> 
> https://forms.gle/cSmPBen2kzEwsrX17
> 
> [UPDATED & OPEN]


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